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2-Methylbenzamide

HCID 10704
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
527-85-5
Standard SMILES
Cc1ccccc1C(N)=O
InChIKey
XXUNIGZDNWWYED-UHFFFAOYSA-N
Molecular formula
C8H9NO
Average molar mass
135.16 g/mol
Monoisotopic mass
135.06841391

Names & identifiers

Preferred name
2-Methylbenzamide
IUPAC
2-methylbenzamide
English name
O-TOLUAMIDE
Molecular formula
C8H9NO
Molecular weight
135.16

Names & synonyms

2-METHYLBENZAMIDEo-Toluamide527-85-5o-Methylbenzamideo-Toluic amideDTXSID602556913WGF92B0HNSC-2169DTXCID905569RefChem:167313208-427-6Benzamide, 2-methyl-
Show more names
o-Toluene amide2-methyl-benzamidFormyl-o-toluidine
o-Tolylamide2-BroMo-4-fluoro-MFCD00007982toluamide1262396-02-02-methyl-benzamide2-Toluamideortho-toluamide

Database identifiers

CAS
527-85-5
PubChem CID
10704
DTXSID
DTXSID6025569
ChEMBL
CHEMBL1489405
UNII
13WGF92B0H
EC Number
208-427-6
Nikkaji
J6.672I

Properties

Computed structural propertiesFilling in

XLogP
0.8
Topological polar surface area
43.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
10
Formal charge
0
Complexity
133

Experimental & physicochemical properties

Solubilityless than 1 mg/mL at 72 °F (NTP, 1992)
Melting Point291 to 297 °F (NTP, 1992)
Vapor Pressure0.000319 [mmHg]
Physical Description · 2 items

2-methylbenzamide is a white powder. (NTP, 1992)

Solid; [Merck Index] Off-white powder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
141 · 141-142 °C (lit.)
Boiling point
248.86 °C · 248.86°C (rough estimate)
Density
1.086 · 1.086
refractive index
1.5589 · 1.5589 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility
alcohol: very soluble(lit.)
pka
16.01 · 16.01±0.50(Predicted)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Fire HazardsFlash point data for this chemical are not available, however it is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: This compound may react violently if exposed to open flame; it should be isolated from all sources of ignition. (NTP, 1992)
Hazards SummaryExplosive; [Merck Index] May cause irritation; Harmful by ingestion; [Sigma-Aldrich MSDS] See alpha-Phenylacetamide.
Reactive GroupAmides and Imides
Reactivity Profile · 1 item

2-METHYLBENZAMIDE is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzamide, 2-methyl-: INACTIVE

Applications

Uses2-Methylbenzamide (o-Toluamide) has been used in total synthesis of phenolic protoberberine alkaloid, cerasonine.

General DescriptionWhite powder.

Upstream & downstream products

Upstream raw materials

2-methylbenzoyl bromideBenzaldehyde, 2-methyl-, oximeo-Toluic acidcarbon monoxide2-Iodotoluene2-Ethyltolueneo-Tolunitrile2-Methylbenzyl cyanide2-Methylbenzaldehyde

Downstream products

3,5-Dinitro-2-methylbenzoic acid(4R)-(-)-2-THIOXO-4-THIAZOLIDINECARBOXYLIC ACID2-Methylbenzyl alcohol2-Methylbenzylamine

Related reactions

12 records
New reaction record
HRID 125617 reaction equation
HRID 125617As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 305564 reaction equation
HRID 305564As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 479492 reaction equation
HRID 479492As reactantuspto-grants-2003_11
HRID 617640 reaction equation
HRID 617640As reactantuspto-grants-1999_09
HRID 673952 reaction equation
HRID 673952As reactantTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 825153 reaction equation
HRID 825153As reactantTest data from https://doi.org/10.1039/C8SC04228D
HRID 1167347 reaction equation
HRID 1167347As reactantuspto-grants-2003_09
HRID 1203512 reaction equation
HRID 1203512As productAs reactantTraining data from https://doi.org/10.1039/C8SC04228D (5/10)
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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Appearance
White to off-white Solid
Merck
13 · 13,9606
InChI
1S/C8H9NO/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3,(H2,9,10)
InChIKey
XXUNIGZDNWWYED-UHFFFAOYSA-N
SMILES
Cc1ccccc1C(N)=O
CAS DataBase Reference
527 · 527-85-5
FDA UNII
13 WGF92B0H · 13WGF92B0H
EPA Substance Registry System
o-Toluamide (527-85-5)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
280 · P280-P305+P351+P338
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22
WGK Germany
3 · 3
TSCA
TSCA listed
HS Code
2924297099 · 2924297099
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety & protection

Fire FightingFires involving this compound can be extinguished using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
hs_code
2924297099
risk_code
22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P280-P305+P351+P338