Butyramide

HCID 10927CAS 541-35-5

Basic information

Standard SMILES
CCCC(N)=O
InChIKey
DNSISZSEWVHGLH-UHFFFAOYSA-N
Molecular formula
C4H9NO
Average molar mass
87.12 g/mol
Monoisotopic mass
87.06841391

Overview

Butanamide is a monocarboxylic acid amide obtained by formal condensation of butanoic acid and ammonia. It is a primary fatty amide and a member of butanamides.

Names & identifiers

Preferred name
Butyramide
IUPAC
butanamide
English name
Butyramide
Molecular formula
C4H9NO
Molecular weight
87.12

Names & synonyms

ButyramideButanamide541-35-5n-ButyramideButanimidic acidN-BUTYLAMIDEButanoic acid, amide9J6OR937VRDTXSID8060248FEMA NO. 4252NSC-8424CHEBI:50724
Show more names
AMIDE C4BusyramideButyricamiden-C3H7C(O)NH2Butyramide,98%
RefChem:122350DTXCID2041595208-776-4butyrylamideButyramidn-butanamideMFCD00041894NSC 8424

Database identifiers

CAS
541-35-5
PubChem CID
10927
DTXSID
DTXSID8060248
ChEMBL
CHEMBL1231396
ChEBI
CHEBI:50724
UNII
9J6OR937VR
EC Number
208-776-4
Nikkaji
J2.639E

Properties

Computed structural properties

XLogP
-0.2
Topological polar surface area
43.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
6

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> Primary amides [FA0801]
SolventsSolvents -> Amides (<C10)
SpringerMaterials PropertiesBoiling point
LogP · 3 items

log Kow = -0.21

-0.21

-0.21

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Physicochemical properties

Melting point
114 · 114-116 °C
Boiling point
216 °C · 216 °C
Density
1.03 · 1.03
refractive index
1.456 · 1.4560
FEMA
4252 · 4252 | BUTYRAMIDE
Flash point
216 °C · 216°C

Safety & regulation

GHS classification

GHS Classification · 4 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.

Hazard information

Regulatory Information · 2 items

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Butanamide: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummarySafe when used as a flavoring agent in food; [JECFA] May cause irritation; [Alfa Aesar MSDS] See Dimethylformamide.
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxicology

Interactions · 3 items

Studies on the effects of antidiuretic hormone (ADH) on diffusion of moderately lipophilic solutes (e.g., butyramide, isobutyramide, & antipyrine, each solute having an oil/water partition > or = 0.0008) across luminal membranes of rabbit cortical collecting tubules, & the effects of ADH on the apparent activation energies (EA, kcal/mol) for water & solute permeation across these tubules revealed that: ADH produced a 60-100% incr in the permeation rates for these solutes, the ADH-dependent apparent EA for water permeation was 9.35 kcal/mol, & the ADH-dependent apparent EA for permeation of moderately lipophilic solutes was in the range 15.8-19.6 kcal/mol. (antidiuretic hormone, Butyramide, Isobutyramide, Antipyrine)

Pyrazole, previously reported to inhibit ethanol oxidation in rats, also effectively blocked the in vivo metab of methanol, propanol, isopropanol, butanol, & isobutanol. Ethanol metab was also inhibited by a variety of oximes & amides, such as butyramide, isobutyramide, acetaldoxime, isobutyraldoxime, & butyraldoxime.

Radioactive tracer & electrolytic techniques were used to study the transport of nonelectrolytes & Na+, respectively, across toad urinary bladders in the presence & absence of antidiuretic hormone (ADH). The permeability of lipophilic mol was roughly proportional to bulk phase oil/water partition coefficients both in the presence & absence of hormone; i.e., ADH elicited a general nonselective incr in the permeation of butyramide & 8 other solutes tested.

Adverse EffectsNeurotoxin - Acute solvent syndrome
Environmental Biodegradation · 2 items

Bench scale activated sludge assay. Fill and draw operation after 6 hrs 1.3% of theoretical oxygen demand; at 12 hrs 3.8% of theoretical oxygen demand; at 24 hr 6.4% of theoretical oxygen demand.

Reverse osmosis yielded 40.5% rejection from 0.01 M soln.

Non-Human Toxicity Excerpts · 1 item

Treatment of Pleurodeles waltlii or Triturus helveticus cleaving eggs with 1M formamide resulted in complete destruction of mitotic spindles; centrospheres were blocked; mitotic pyknosis with disappearance of nuclei was observed. Pluripolar mitoses in which asters were separated from spindles occurred in Pleurodeles eggs treated with 0.5M formamide. In a comparative study with acetamide, propionamide, & butyramide, the effect on T. helveticus eggs was observed at smaller concn with increasing number of C atoms in the mol.

Antidote and Emergency Treatment · 2 items

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
hs_code
29241900
risk_code
22
Signal word
Warning

Chemistry & industry

Pharmacology

Absorption, Distribution and Excretion · 1 item

Lung endothelial permeabilities were determined by injecting butyramide & other test substances into the jugular vein of anesthetized dogs, followed by analysis of sequential blood samples from the carotid artery. The mathematically derived permeability surface product for butyramide was 42.

Cellular LocationsCytoplasm

Uses & manufacturing

UsesUsed as a flavoring agent; [JECFA]
Methods of Manufacturing · 4 items

Prepn: ...by a modified Willgerodt reaction.

Prepn: ...from butyronitrile.

Prepn: ... from butyryl chloride.

Prepn: ... from butyric acid.

Use Classification · 2 items

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 2 items

Butanamide: ACTIVE

N-BUTYLAMIDE WAS NOT AN EFFECTIVE CRYOPROTECTANT FOR RABBIT SEMEN.

Applications · 1 item

UsesButyramide was used in the synthesis of hydroxamic acids, electrorheological fluids and β-amodoorganotin compounds. It was used as substrate of (+)-γ-lactamase to develop a microreactor to study enzyme stability, activity, kinetics and substrate specificity.

Preparation methods · 1 item

PreparationButyramide is prepared by amination of n-butyric acid. n-Butyric acid is heated with ammonia gas bubbled through it, and the reaction mixture reaches 200–215°C after approximately 40 hours. Heating and ammonia flow are then stopped, and the mixture is cooled below 20°C before filtration to yield butyramide.An alternative method involves reacting n-butyric acid with urea: First, heat a mixture of 8 kg of n-butyric acid and 3 kg of urea under reflux for 10 hours. Allow the mixture to cool to 70–80°C, then add a suitable amount of hot ethanol. Decolorize the hot solution, filter it while hot, and cool. The crude product obtained by filtration is recrystallised from ethanol to yield the final product.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
廊坊乾耀科技有限公司0316-2617888 17301291189 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Additional notes

DefinitionChEBI: Butanamide is a monocarboxylic acid amide obtained by formal condensation of butanoic acid and ammonia. It is a primary fatty amide and a member of butanamides.

Related reactions

14 records

Linked notes

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