Author Topic: H-NMR of 2c-b  (Read 1055 times)

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phenyl

  • Guest
H-NMR of 2c-b
« on: April 16, 2002, 06:40:00 PM »
Wondering if anyone has a H-NMR or C-NMR spectra of 2c-b.  The NMR for the precursor nitrostyrene would also be usefull.  They are straightforward but comparison to published or other is always nice.  thank you.

Rhodium

  • Guest
2C-B MSDS
« Reply #1 on: April 16, 2002, 10:17:00 PM »
I don't think I can dig up any graphical representations of the NMR spectrum of the nitrostyrene, but that should not be necessary - you would have to be a complete arch-moron if you would not recognize 2,5-dimethoxy-ß-nitrostyrene when you see it (bright orange, and negligible solubility in room-temp IPA).

While I dig among my references, enjoy the MSDS for 2C-B I just downloaded from Sigma-Aldrich.

"EXPOSURE CAN CAUSE DISORDERS OF VISUAL PERCEPTION, EXTREME ALTERATIONS OF MOOD, DEPRESSION, DISTORTION OF BODY IMAGE, DEPERSONALIZATION, DISORDERS OF THOUGHT AND TIME SENSE, ANXIETY, NAUSEA, VOMITING AND VARIABLE EFFECTS ON HEART-RATE AND BLOOD PRESSURE."

             M A T E R I A L  S A F E T Y  D A T A  S H E E T
            
SECTION 1. - - - - - - - - - CHEMICAL IDENTIFICATION- - - - - - - - - -
    CATALOG #:            B159
    NAME:                 (+/-) 1-(4-BROMO-2,5-DIMETHOXYPHENYL)-ETHYLAMINE

SECTION 2. - - - - - COMPOSITION/INFORMATION ON INGREDIENTS - - - - - -
    CAS #: 66142-81-2
    MF: C10H14BRNO2

SECTION 3. - - - - - - - - - - HAZARDS IDENTIFICATION - - - - - - - - -
  LABEL PRECAUTIONARY STATEMENTS
    HIGHLY TOXIC (USA)
    VERY TOXIC (EU)
    VERY TOXIC BY INHALATION, IN CONTACT WITH SKIN AND IF SWALLOWED.
    TARGET ORGAN(S):
    CENTRAL NERVOUS SYSTEM
    IN CASE OF ACCIDENT OR IF YOU FEEL UNWELL, SEEK MEDICAL ADVICE
    IMMEDIATELY (SHOW THE LABEL WHERE POSSIBLE).
    WEAR SUITABLE PROTECTIVE CLOTHING, GLOVES AND EYE/FACE
    PROTECTION.
    DO NOT BREATHE DUST.

SECTION 4. - - - - - - - - - - FIRST-AID MEASURES- - - - - - - - - - -
    IF SWALLOWED, WASH OUT MOUTH WITH WATER PROVIDED PERSON IS CONSCIOUS.
    CALL A PHYSICIAN IMMEDIATELY.
    IF INHALED, REMOVE TO FRESH AIR. IF NOT BREATHING GIVE ARTIFICIAL
    RESPIRATION. IF BREATHING IS DIFFICULT, GIVE OXYGEN.
    IN CASE OF SKIN CONTACT, FLUSH WITH COPIOUS AMOUNTS OF WATER
    FOR AT LEAST 15 MINUTES. REMOVE CONTAMINATED CLOTHING AND
    SHOES. CALL A PHYSICIAN.
    IN CASE OF CONTACT WITH EYES, FLUSH WITH COPIOUS AMOUNTS OF WATER
    FOR AT LEAST 15 MINUTES. ASSURE ADEQUATE FLUSHING BY SEPARATING
    THE EYELIDS WITH FINGERS. CALL A PHYSICIAN.

SECTION 5. - - - - - - - - - FIRE FIGHTING MEASURES - - - - - - - - - -
  EXTINGUISHING MEDIA
    WATER SPRAY.
    CARBON DIOXIDE, DRY CHEMICAL POWDER OR APPROPRIATE FOAM.
  SPECIAL FIREFIGHTING PROCEDURES
    WEAR SELF-CONTAINED BREATHING APPARATUS AND PROTECTIVE CLOTHING TO
    PREVENT CONTACT WITH SKIN AND EYES.
  UNUSUAL FIRE AND EXPLOSIONS HAZARDS
    EMITS TOXIC FUMES UNDER FIRE CONDITIONS.

SECTION 6. - - - - - - - - ACCIDENTAL RELEASE MEASURES- - - - - - - - -
    WEAR SELF-CONTAINED BREATHING APPARATUS, RUBBER BOOTS AND HEAVY
    RUBBER GLOVES.
    SWEEP UP, PLACE IN A BAG AND HOLD FOR WASTE DISPOSAL.
    AVOID RAISING DUST.
    VENTILATE AREA AND WASH SPILL SITE AFTER MATERIAL PICKUP IS COMPLETE.
    EVACUATE AREA.

SECTION 8. - - - - - - EXPOSURE CONTROLS/PERSONAL PROTECTION- - - - - -
    SAFETY SHOWER AND EYE BATH.
    USE ONLY IN A CHEMICAL FUME HOOD.
    WASH CONTAMINATED CLOTHING BEFORE REUSE.
    WASH THOROUGHLY AFTER HANDLING.
    DO NOT BREATHE DUST.
    DO NOT GET IN EYES, ON SKIN, ON CLOTHING.
    AVOID PROLONGED OR REPEATED EXPOSURE.
    NIOSH/MSHA-APPROVED RESPIRATOR.
    COMPATIBLE CHEMICAL-RESISTANT GLOVES.
    CHEMICAL SAFETY GOGGLES.
    KEEP TIGHTLY CLOSED.
    STORE IN A COOL DRY PLACE.

SECTION 9. - - - - - - - PHYSICAL AND CHEMICAL PROPERTIES - - - - - - -
  APPEARANCE AND ODOR
    SOLID.
  PHYSICAL PROPERTIES
    MELTING POINT:      234 - 235  C
    SOLUBILITY:
           WATER -Z1076

SECTION 10. - - - - - - - - -STABILITY AND REACTIVITY - - - - - - - - -
  STABILITY
    STABLE.
  INCOMPATIBILITIES
    STRONG OXIDIZING AGENTS
  HAZARDOUS COMBUSTION OR DECOMPOSITION PRODUCTS
    CARBON MONOXIDE, CARBON DIOXIDE
    NITROGEN OXIDES
    HYDROGEN CHLORIDE GAS
    HYDROGEN BROMIDE GAS
  HAZARDOUS POLYMERIZATION
    WILL NOT OCCUR.

SECTION 11. - - - - - - - - - TOXICOLOGICAL INFORMATION - - - - - - - -
  ACUTE EFFECTS
    MAY CAUSE SKIN IRRITATION.
    MAY BE FATAL IF ABSORBED THROUGH SKIN.
    MAY CAUSE EYE IRRITATION.
    MAY BE FATAL IF INHALED.
    MATERIAL MAY BE IRRITATING TO MUCOUS MEMBRANES AND UPPER
    RESPIRATORY TRACT.
    MAY BE FATAL IF SWALLOWED.
    EXPOSURE CAN CAUSE DISORDERS OF VISUAL PERCEPTION, EXTREME ALTERATIONS
    OF MOOD, DEPRESSION, DISTORTION OF BODY IMAGE, DEPERSONALIZATION,
    DISORDERS OF THOUGHT AND TIME SENSE, ANXIETY, NAUSEA, VOMITING AND
    VARIABLE EFFECTS ON HEART-RATE AND BLOOD PRESSURE.
  CHRONIC EFFECTS
    TARGET ORGAN(S):
    CENTRAL NERVOUS SYSTEM

SECTION 13. - - - - - - - - - DISPOSAL CONSIDERATIONS - - - - - - - - -
    CONTACT THE DRUG ENFORCEMENT ADMINISTRATION CONCERNING THE DISPOSAL
    OF CONTROLLED SUBSTANCES.
    OBSERVE ALL FEDERAL, STATE AND LOCAL ENVIRONMENTAL REGULATIONS.

SECTION 15. - - - - - - - - - REGULATORY INFORMATION - - - - - - - - - -
  EUROPEAN INFORMATION
    CAUTION: SUBSTANCE NOT YET FULLY TESTED.
    VERY TOXIC
    R 26/27/28
    VERY TOXIC BY INHALATION, IN CONTACT WITH SKIN AND IF SWALLOWED.
    S 45
    IN CASE OF ACCIDENT OR IF YOU FEEL UNWELL, SEEK MEDICAL ADVICE
    IMMEDIATELY (SHOW THE LABEL WHERE POSSIBLE).
    S 36/37/39
    WEAR SUITABLE PROTECTIVE CLOTHING, GLOVES AND EYE/FACE
    PROTECTION.
    S 22
    DO NOT BREATHE DUST.

yellium

  • Guest
>IN CASE OF ACCIDENT OR IF YOU FEEL UNWELL, ...
« Reply #2 on: April 17, 2002, 09:04:00 PM »
>IN CASE OF ACCIDENT OR IF YOU FEEL UNWELL,

Not bloody likely that will happen.

yellium

  • Guest
BTW, proton NMR of phenethylamines is so easy ...
« Reply #3 on: April 17, 2002, 09:11:00 PM »
BTW, proton NMR of phenethylamines is so easy it's a shame.

Have to guess the actual NMR shifts, because I don't have the datafiles anymore, only printouts. Anyway, here goes:

Solvent (wet) MeOD

2.84 triplet, 2H (CH2 next to amine)
3.08 triplet, 2H (CH2 next to aromatic ring)
3.80 doublet, 6H (OMe)
6.90 singlet, 1H (Ar-H)
7.12 singlet, 1H (Ar-H)

NMR shifts are +/- 0.03.

yellium

  • Guest
More NMR data of other compounds: Ar-H Ar-H OMe ...
« Reply #4 on: April 17, 2002, 11:18:00 PM »

More NMR data of other compounds:


      Ar-H  Ar-H    OMe   CH2  CH2
2CC  7.00   6.90   3.78  3.08  2.88
2CB  7.17   6.83   3.71  3.09  2.80
2CI  7.29   8.84   3.78  3.10  2.84

2CT2 6.80   6.81   3.77  3.04  2.82
CH3 from CH3CH2S: 1.06  triplet, 3H
CH2 from CH3CH2S overlaps with CH2 at 2.84

2CT7 6.84   6.86   3.78  3.06  2.85
-CH2- from CH3CH2CH2S: 1.60, sixtet(??) 2H
-CH3 from CH3CH2CH2S: 0.84, triplet 3H
-SCH2 from CH3CH2CH2S overlaps with CH2 at 2.85.

DOB:
7.09, singlet 1H singelAr-H
6.84, singlet 1H Ar-H
3.78, doublet 6H OMe
3.62, quartet 1H CH
2.82, doublet 2H CH2
1.08. doublet 3H CH3

karel

  • Guest
2CB NMR
« Reply #5 on: April 18, 2002, 09:16:00 PM »
Long time ago, SWIM recorded spectra of this compound...

2CB freebase
1H NMR (CDCl3,400MHz) 7.02 (s,1H), 6.74 (s,1H), 3.84 (s,3H), 3.77 (s,3H), 2.90 (t,J=6.9Hz,2H), 2.72 (t,J=6.9Hz,2H), 1.35 (broad s,2H)
13C NMR (CDCl3,100MHz) 151.9 (s), 149.6 (s), 128.3 (s), 115.7 (d), 114.8(d), 108.8 (s), 56.9 (q), 56.0 (q), 42.1 (t), 34.9 (t)
2CB hydrochloride
1H NMR (D2O,400MHz) 7.14 (s,1H), 6.88 (s,1H), 3.78 (s,3H), 3.74 (s,3H), 3.17 (t,J=6.9Hz,2H), 2.88 (t,J=6.9Hz,2H)

Regards,

karel

Rhodium

  • Guest
Analytical profile of 2C-B
« Reply #6 on: April 19, 2002, 05:29:00 AM »
The analytical article dealing with 2C-B and its geometrical isomers I had never contained any NMR data, but there is a lot of other data in it: J Chrom Sci 36, 23-28 (1998)

From J Anal Toxicol, Vol 22, No 5, pp 345–354 (1998), which I unfortunately don't have: "This study sought to identify, by means of several analytical methods (GC–MS, HPLC–DAD, CE–DAD, FTIR, and NMR), 4-bromo-2,5-dimethoxyphenethylamine (2C-B), which was found in two sets of tablets obtained from the Swiss black market. Unequivocal identification of 2C-B was only achieved by a combination of mass spectrometric and NMR analysis."

According to J Chrom Sci 33, 583-590 (1995), when subjected to FTIR spectroscopy, 2C-B shows characteristic absorption bands at 1039, 1210, 1381 and 1491 cm-1.

Finally, here is the MS spectrum of 2C-B (taken from

http://jhs.pharm.or.jp/48%281%29/48_14.pdf

: