766-91-6

Basic information

• Product Name: Benzene, (diazomethyl)-
• Synonyms: Benzene, (diazomethyl)-;(Diazomethyl)benzene;Diazo(phenyl)methane;Diazomethylbenzene;Diazophenylmethane;Phenyldiazomethane;α-Diazotoluene
• CAS NO: 766-91-6
• Molecular Formula: C₇H₆N₂
• Molecular Weight: 118.1359
• Mol File: 766-91-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: Benzene, (diazomethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (diazomethyl)-(766-91-6)
• EPA Substance Registry System: Benzene, (diazomethyl)-(766-91-6)

Safety Data

• Hazardous Substances Data: 766-91-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 7, p. 438, 1990The Journal of Organic Chemistry, 28, p. 592, 1963 DOI: 10.1021/jo01037a523

InChI:InChI=1/C7H6N2/c8-9-6-7-4-2-1-3-5-7/h1-6H

Synthetic route

5-Phenyl-1H-tetrazole (18039-42-4) → phenyldiazomethane (766-91-6)

Conditions	Yield
at -261.16℃; for 0.0166667h; Ar matrix photolysis;

5-phenyl-2H-1,2,3,4-tetrazole (18039-42-4) → N-phenylcarbodiimide (29872-49-9) + 3-phenyl-1H-diazirine + 1-phenylcyanamide (622-34-4) + phenyldiazomethane (766-91-6)

Conditions	Yield
at -253.16℃; Temperature; Irradiation;

2-{(1R,2R)-2-Acetylamino-1-[(S)-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3,3-diethoxy-propoxy}-propionic acid (70279-98-0) + phenyldiazomethane (766-91-6) → 2-{(1R,2R)-2-Acetylamino-1-[(S)-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3,3-diethoxy-propoxy}-propionic acid benzyl ester (77120-45-7)

phenyldiazomethane (766-91-6) → stilbene (588-59-0)

Conditions	Yield
In tert-butyl alcohol at -196℃; Irradiation;	17.0 % Chromat.

phenyldiazomethane (766-91-6) → 4-O-(N-acetyl-3,4,6-tri-O-benzyl-β-D-glucosaminyl)-N-acetylmuramic acid benzyl ester

Conditions	Yield
Multi-step reaction with 2 steps 2: 53 percent / 60percent aqueous acetic acid / 1.17 h / 60 °C View Scheme

phenyldiazomethane (766-91-6) → 4-O-(N-acetyl-3,4,6-tri-O-benzyl-β-D-glucosaminyl)-6-O-2-tetradecylhexadecanoyl-N-acetylmuramic acid benzyl ester

Conditions	Yield
Multi-step reaction with 3 steps 2: 53 percent / 60percent aqueous acetic acid / 1.17 h / 60 °C 3: 70 percent / dicyclohexylcarbodiimide, 4-(N,N-dimethylamino)pyridine, 1-hydroxybenzotriazole View Scheme

Upstream product

• 18039-42-4 5-Phenyl-1H-tetrazole 
• 18039-42-4 5-phenyl-2H-1,2,3,4-tetrazole 

Downstream Products

• 77120-45-7 2-{(1R,2R)-2-Acetylamino-1-[(S)-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3,3-diethoxy-propoxy}-propionic acid benzyl ester 
• 588-59-0 stilbene 

Relevant articles and documents

Bond-shift isomers: The co-existence of allenic and propargylic phenylnitrile imines

We discovered a 1,3-dipolar species co-existing in two different structures. Photolysis of matrix-isolated 5-phenyltetrazole generates two forms of phenylnitrile imine: propargylic and allenic. They are not resonance structures but correspond to different energy minima, representing bond-shift isomers. These distinct species were characterized spectroscopically and confirmed by calculations up to the CASSCF(14,12) theory level.