Reactant BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Preparation
Reagent sodium methylate
Other Conditions Erwaermen des Reaktionsprodukts mit Salzsaeure
Note 1 Handbook
Ref. 1 501525; Patent; Hesse; DE 88224; FTFVA6; Fortschr.Teerfarbenfabr.Verw.Industriezweige; DE; GE; 4; 1291.
Ref. 2 500436; Journal; Wallach; Pond; CHBEAM; Chem.Ber.; 28; 1895; 2719.
Ref. 3 500362; Journal; Hoering; CHBEAM; Chem.Ber.; 38; 1905; 3469; CHZEA6; Chem.Zentralbl.; GE; 77; II; 1906; 1223.
Reaction ID 741015
Reactant BRN 6224 benzo[1,3]dioxole-5-carbonitrile
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Preparation
Reagent ethyl magnesium bromide
diethyl ether
Other Conditions Erwaermen des erhaltenen 1-Benzo<1,3>dioxol-5-yl-propan-1-on-imins mit wss. Salzsaeure
Note 1 Handbook
Ref. 1 1997615; Journal; Fuson; Gaertner; Chadwick; JOCEAH; J.Org.Chem.; 13; 1948; 489, 493.
Reaction 15 of 34
Reaction ID 809025
Reactant BRN 82640 5-propenyl-benzo[1,3]dioxole
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Preparation
Reagent phosphorus-pentachloride
Other Conditions Zerlegung des Produkts mit Wasser und Kochen des mit Wasserdampf ueberdestillierten Oels mit alkoholischer Kalilauge
Note 1 Handbook
Ref. 1 500346; Journal; Schimmel & Co.; CHZEA6; Chem.Zentralbl.; GE; 76; I; 1905; 1470.
Ref. 2 501534; Book Review / Secondary Ref.; Schimmel & Co.; Bericht vom April 1905, 49.
Reaction 16 of 34
Reaction ID 1651712
Reactant BRN 115506 benzo[1,3]dioxole
385632 propionyl chloride
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Preparation
Yield 58 percent (BRN=165729)
Reagent SnCl4
Solvent CH2Cl2
Time 1 hour(s)
Temperature 20 C
Ref. 1 5702207; Journal; Daukshas, V. K.; Gaidyalis, P. G.; Pyatrauskas, O. Yu.; Udrenaite, E. B.; Gasperavichene, G. A.; Raguotene, N. V.; PCJOAU; Pharm.Chem.J.(Engl.Transl.); EN; 21; 5; 1987; 341-345; KHFZAN; Khim.Farm.Zh.; RU; 21; 5; 1987; 569-573.
Reaction 17 of 34
Reaction ID 1802483
Reactant BRN 150197 1-benzo[1,3]dioxol-5-yl-propan-1-ol
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Preparation
Yield 64.06 percent (BRN=165729)
Reagent chromium trioxide, concentrated H2SO4
Solvent H2O
acetone
Time 3 hour(s)
Temperature 0 - 20 C
Ref. 1 5677213; Journal; Alesso, Elba N.; Tombari, Dora G.; Iglesias, Graciela Y. Moltrasio; Aguirre, Jose M.; CJCHAG; Can.J.Chem.; EN; 65; 1987; 2568-2574.
Reaction 18 of 34
Reaction ID 1838008
Reactant BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
1098229 methanol
Product BRN 155294 5-(1-methoxy-propyl)-benzo[1,3]dioxole
No. of Reaction Details 1
Reaction Classification Preparation
Yield 81 percent (BRN=155294)
Reagent NaBH4
Time 30 min
Temperature 20 C
Ref. 1 5519586; Journal; Daukshas, V. K.; Gaidyalis, P. G.; Udrenaite, E. B.; Labanauskas, L. K.; Gasperavichene, G. A.; et al.; PCJOAU; Pharm.Chem.J.(Engl.Transl.); EN; 23; 12; 1989; 990-995; KHFZAN; Khim.Farm.Zh.; RU; 23; 12; 1989; 1466-1470.
Reaction 19 of 34
Reaction ID 1838009
Reactant BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
505995 formamide
Product BRN 5540275 N-1-(3,4-dimethoxyphenyl)propylformamide
No. of Reaction Details 1
Reaction Classification Preparation
Yield 52.2 percent (BRN=5540275)
Time 8 hour(s)
Temperature 180 - 190 C
Ref. 1 5677213; Journal; Alesso, Elba N.; Tombari, Dora G.; Iglesias, Graciela Y. Moltrasio; Aguirre, Jose M.; CJCHAG; Can.J.Chem.; EN; 65; 1987; 2568-2574.
Reaction 20 of 34
Reaction ID 1838010
Reactant BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
Product BRN 150197 1-benzo[1,3]dioxol-5-yl-propan-1-ol
No. of Reaction Details 2
Reaction Classification Preparation
Yield 90 percent (BRN=150197)
Reagent LiAlH4
Solvent diethyl ether
Time 30 min
Other Conditions Heating
Ref. 1 5519586; Journal; Daukshas, V. K.; Gaidyalis, P. G.; Udrenaite, E. B.; Labanauskas, L. K.; Gasperavichene, G. A.; et al.; PCJOAU; Pharm.Chem.J.(Engl.Transl.); EN; 23; 12; 1989; 990-995; KHFZAN; Khim.Farm.Zh.; RU; 23; 12; 1989; 1466-1470.
Reaction ID 3824784
Reactant BRN 82642 5-trans-propenyl-benzo[1,3]dioxole
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
164033 benzo[1,3]dioxol-5-yl-propan-2-one
No. of Reaction Details 3
Reaction Classification Chemical behaviour
Yield 18 percent (BRN=165729)
60 percent (BRN=164033)
Reagent O2
Catalyst PdCl2/CuCl
Solvent dimethylformamide
H2O
Time 10 hour(s)
Temperature 50 C
Other Conditions Reagents
Subject Studied Product distribution
Ref. 1 5618292; Journal; Nagashima, Hideo; Sato, Koji; Tsuji, Jiro; TETRAB; Tetrahedron; EN; 41; 23; 1985; 5645-5652.
Reaction 23 of 34
Reaction ID 5261935
Reactant BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
Product BRN 8406937 1-benzo[1,3]dioxol-5-yl-2-chloro-propan-1-one
No. of Reaction Details 1
Yield 66 percent (BRN=8406937)
Reaction Classification Preparation
Reagent CuCl2*2H2O
LiCl
Solvent dimethylformamide
Time 6 hour(s)
Temperature 80 C
Reaction Type Chlorination
Ref. 1 6206531; Journal; Zacchino, Susana A.; Lopez, Silvia N.; Pezzenati, German D.; Furlan, Ricardo L.; Santecchia, Carina B.; Munoz, Lorena; Giannini, Fernando A.; Rodriguez, Ana M.; Enriz, Ricardo D.; JNPRDF; J.Nat.Prod.; EN; 62; 10; 1999; 1353 - 1357.
Reaction 24 of 34
Reaction ID 5457190
Reactant $a-<3.4-methylenedioxy-phenyl>-allylene
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Preparation (half reaction)
Reagent aqueous-alcoholic sulfuric acid
Note 1 Handbook
Ref. 1 500305; Journal; Foulds; Robinson; JCSOA9; J.Chem.Soc.; 105; 1914; 1966.
Reaction 26 of 34
Reaction ID 5457192
Reactant 1%1&-ethoxy-isosafrole
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Preparation (half reaction)
Reagent hydrochloric acid
Note 1 Handbook
Ref. 1 500362; Journal; Hoering; CHBEAM; Chem.Ber.; 38; 1905; 3469; CHZEA6; Chem.Zentralbl.; GE; 77; II; 1906; 1223.
Reaction 27 of 34
Reaction ID 5457193
Reactant 1%1&-methoxy-isosafrole
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Preparation (half reaction)
Reagent diluted hydrochloric acid
Note 1 Handbook
Ref. 1 500428; Journal; Tiffeneau; BSCFAS; Bull.Soc.Chim.Fr.; <4> 1; 1907; 1212.
Reactant 1%1&-methoxy-isosafrole
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Preparation (half reaction)
Reagent diluted hydrochloric acid
Note 1 Handbook
Ref. 1 500428; Journal; Tiffeneau; BSCFAS; Bull.Soc.Chim.Fr.; <4> 1; 1907; 1212.
Reaction 28 of 34
Reaction ID 5457194
Reactant BRN 2037554 sulfuric acid
135259 5-prop-1-ynyl-benzo[1,3]dioxole
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Chemical behaviour
Note 1 Handbook
Ref. 1 504625; Book Review / Secondary Ref.; Robinson; Priv.-Mitt..
Reaction 29 of 34
Reaction ID 5457195
Reactant BRN 2036449 2-methyl-2-trideuteriomethoxy-propane
82640 5-propenyl-benzo[1,3]dioxole
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Chemical behaviour
Other Conditions Zerlegung des Reaktionsprodukts mit Wasser und Kochen des mit Wasserdampf destillierten Oels mit alkoh. Kalilauge
Note 1 Handbook
Ref. 1 500429; Book Review / Secondary Ref.; Schimmel & Co.; Bericht vom April 1905, 49; C. 1905 I, 1470.
Reaction 30 of 34
Reaction ID 5457196
Reactant BRN 1098214 hydrochloric acid
9790 1$x-ethoxy-1$x-benzo[1,3]dioxol-5-yl-propene
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Chemical behaviour
Note 1 Handbook
Ref. 1 500362; Journal; Hoering; CHBEAM; Chem.Ber.; 38; 1905; 3469; CHZEA6; Chem.Zentralbl.; GE; 77; II; 1906; 1223.
Reaction 31 of 34
Reaction ID 5457197
Reactant chromic acid
Reactant BRN 150197 1-benzo[1,3]dioxol-5-yl-propan-1-ol
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Chemical behaviour
Note 1 Handbook
Ref. 1 500348; Journal; Mameli; AANLAW; Atti Accad.Naz.Lincei Cl.Sci.Fis.Mat.Nat.Rend.; <5> 13 II; 1904; 320; GCITA9; Gazz.Chim.Ital.; 34 II; 1904; 416.
--------------------------------
Melting Point 1-7 of 7
45 - 46 hexane 1
39 1 2-3
38 2 4
38.5 3 5
38 hexane 4 6
38 - 39 5 7
36 - 37 8
Note 1 Handbook
Note 2 Handbook
Note 3 Handbook
Note 4 Handbook
Note 5 Handbook
Ref. 1 5702207; Journal; Daukshas, V. K.; Gaidyalis, P. G.; Pyatrauskas, O. Yu.; Udrenaite, E. B.; Gasperavichene, G. A.; Raguotene, N. V.; PCJOAU; Pharm.Chem.J.(Engl.Transl.); EN; 21; 5; 1987; 341-345; KHFZAN; Khim.Farm.Zh.; RU; 21; 5; 1987; 569-573.
Ref. 2 501525; Patent; Hesse; DE 88224; FTFVA6; Fortschr.Teerfarbenfabr.Verw.Industriezweige; DE; GE; 4; 1291.
Ref. 3 500436; Journal; Wallach; Pond; CHBEAM; Chem.Ber.; 28; 1895; 2719.
Ref. 4 735496; Journal; Angeli; GCITA9; Gazz.Chim.Ital.; 22 II; 1892; 479; CHBEAM; Chem.Ber.; 25; 1892; 1960.
Ref. 5 504175; Journal; Ciamician; Silber; GCITA9; Gazz.Chim.Ital.; 23 II; 1893; 195, 202; GCITA9; Gazz.Chim.Ital.; 24 I; 1894; 431, 541.
Ref. 6 514935; Journal; Hillmer; Schorning; ZPCLAH; Z.Phys.Chem.(Leipzig);
168; 1934; 81, 104.
Ref. 7 1997615; Journal; Fuson; Gaertner; Chadwick; JOCEAH; J.Org.Chem.; 13; 1948; 489, 493.
Ref. 8 5677213; Journal; Alesso, Elba N.; Tombari, Dora G.; Iglesias, Graciela Y. Moltrasio; Aguirre, Jose M.; CJCHAG; Can.J.Chem.; EN; 65; 1987; 2568-2574.
-----------------------
Boiling Point 1-2 of 2
153 - 154 13 1 1-2
128 3.5 2 3
Note 1 Handbook
Note 2 Handbook
Ref. 1 501525; Patent; Hesse; DE 88224; FTFVA6; Fortschr.Teerfarbenfabr.Verw.Industriezweige; DE; GE; 4; 1291.
Ref. 2 500436; Journal; Wallach; Pond; CHBEAM; Chem.Ber.; 28; 1895; 2719.
Ref. 3 519826; Patent; Winthrop Chem. Co.; US 1964973; 1932.
--------------
CAS Registry Number 41103-34-8
Chemical Name 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
Isosafroldibromid
Autoname 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
Molecular Formula C10H10Br2O2
Molecular Weight 322.00
Melting Point 1-4 of 4
51 1 1
52 - 53 2 2-3
52 - 53 3 2
51 - 52 pentane 4 4
Note 1 Handbook
Note 2 Handbook
Note 3 Handbook
Note 4 Handbook
Ref. 1 500366; Journal; Hoering; Baum; CHBEAM; Chem.Ber.; 42; 1909; 3080.
Ref. 2 500364; Journal; Waterman; Priester; RTCPA3; Recl.Trav.Chim.Pays-Bas; 48; 1929; 941.
Ref. 3 1534557; Journal; Mannich; ARPMAS; Arch.Pharm.(Weinheim Ger.); 248; 1910; 143; CHZEA6; Chem.Zentralbl.; GE; 80; I; 1909; 923.
Ref. 4 512137; Journal; Naves; Ardizio; BSCFAS; Bull.Soc.Chim.Fr.; 1957; 1053, 1056.
Reaction 5 of 20
Reaction ID 186589
Reactant BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
Product BRN 135259 5-prop-1-ynyl-benzo[1,3]dioxole
No. of Reaction Details 1
Reaction Classification Preparation
Reagent diethylene glycol
potassium hydroxide
Note 1 Handbook
Ref. 1 512718; Journal; Nelb; Tarbell; JACSAT; J.Amer.Chem.Soc.; 71; 1949; 2936.
Reaction 6 of 20
Reaction ID 186590
Reactant BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
Product BRN 150217 5-(2-bromo-propenyl)-benzo[1,3]dioxole
No. of Reaction Details 1
Reaction Classification Preparation
Other Conditions Bei der Destillation unter vermindertem Druck
Note 1 Handbook
Ref. 1 500305; Journal; Foulds; Robinson; JCSOA9; J.Chem.Soc.; 105; 1914; 1966.
Reaction 7 of 20
Reaction ID 186591
Reactant BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Preparation
Reagent sodium methylate
Other Conditions Erwaermen des Reaktionsprodukts mit Salzsaeure
Note 1 Handbook
Ref. 1 501525; Patent; Hesse; DE 88224; FTFVA6; Fortschr.Teerfarbenfabr.Verw.Industriezweige; DE; GE; 4; 1291.
Ref. 2 500436; Journal; Wallach; Pond; CHBEAM; Chem.Ber.; 28; 1895; 2719.
Ref. 3 500362; Journal; Hoering; CHBEAM; Chem.Ber.; 38; 1905; 3469; CHZEA6; Chem.Zentralbl.; GE; 77; II; 1906; 1223.
Reaction 8 of 20
Reaction ID 186592
Reactant BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
Product BRN 171391 1-benzo[1,3]dioxol-5-yl-2-bromo-propan-1-ol
No. of Reaction Details 2
Reaction Classification Preparation
Reagent aqueous acetone
marble
Note 1 Handbook
Ref. 1 500356; Patent; Hoering; DE 174496.
Ref. 2 500362; Journal; Hoering; CHBEAM; Chem.Ber.; 38; 1905; 3469; CHZEA6; Chem.Zentralbl.; GE; 77; II; 1906; 1223.
Reaction 9 of 20
Reaction ID 809028
Reactant BRN 82640 5-propenyl-benzo[1,3]dioxole
Product BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
No. of Reaction Details 3
Reaction Classification Preparation
Reagent diethyl ether
bromine
Note 1 Handbook
Ref. 1 500360; Journal; Wallach; Pond; CHBEAM; Chem.Ber.; 38; 1905; 2719.
Reaction 14 of 20
Reaction ID 5400404
Reactant BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
Product 1%2&-bromo-isosafrole
No. of Reaction Details 1
Reaction Classification Chemical behaviour (half reaction)
Other Conditions Bei der Destillation unter vermindertem Druck
Note 1 Handbook
Ref. 1 500305; Journal; Foulds; Robinson; JCSOA9; J.Chem.Soc.; 105; 1914; 1966.
Reaction 15 of 20
Reaction ID 5461129
Reactant BRN 3587193 Br2
1696894 diethyl ether
82640 5-propenyl-benzo[1,3]dioxole
Product BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
No. of Reaction Details 1
Reaction Classification Chemical behaviour
Note 1 Handbook
Ref. 1 500436; Journal; Wallach; Pond; CHBEAM; Chem.Ber.; 28; 1895; 2719.
Reaction 16 of 20
Reaction ID 5461130
Reactant cis-isosafrole
Product BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
No. of Reaction Details 1
Reaction Classification Preparation (half reaction)
Reagent diethyl ether
bromine
Note 1 Handbook
Ref. 1 512137; Journal; Naves; Ardizio; BSCFAS; Bull.Soc.Chim.Fr.; 1957; 1053, 1056.
Reaction 17 of 20
Reaction ID 5461132
Reactant trans-isosafrole
Product BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
No. of Reaction Details 1
Reaction Classification Preparation (half reaction)
Reagent diethyl ether
bromine
Temperature -10 C
Note 1 Handbook
Ref. 1 512137; Journal; Naves; Ardizio; BSCFAS; Bull.Soc.Chim.Fr.; 1957; 1053, 1056.
Reaction 18 of 20
Reaction ID 5574136
Reactant BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
Reactant isosafrole bromohydrin
Product BRN 357396 bis-(1-benzo[1,3]dioxol-5-yl-2-bromo-propyl)-ether
No. of Reaction Details 1
Reaction Classification Preparation
Other Conditions im verschlossenen Gefaess
Note 1 Handbook
Ref. 1 969731; Journal; Mannich; Schmitt; ARPMAS; Arch.Pharm.(Weinheim Ger.); 1928; 80; CHZEA6; Chem.Zentralbl.; GE; 98; I; 1927; 951.
Reaction 19 of 20
Reaction ID 5574947
Reactant BRN 171390 5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
Product 1%2&-bromo-isosafrole
Product BRN 3587158 hydrogen bromide
No. of Reaction Details 1
Reaction Classification Chemical behaviour
Note 1 Handbook
Ref. 1 500364; Journal; Waterman; Priester; RTCPA3; Recl.Trav.Chim.Pays-Bas; 48; 1929; 941.