Butylated hydroxytoluene is an antioxidant widely used in foods and in food-related products. Butylated hydroxytoluene is a Ferroptosis inhibitor.

Synonyms: BHT; NSC 6347

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Quality Control of Butylated hydroxytoluene Purity: 98% SDS Specification

COA

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NMR

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Product Citations

Synthetic Elaboration of β-Carbonyl Alkylboronic Esters

Hamilton, Mason D ;

Abstract: Organoboron compounds are some of the most synthetically versatile compounds in organic chemistry due to the many valuable transformations of the C-B bond. This synthetic versatility combined with the pharmacophoric nature of carboxylic acids has led to an increased interest in the one-pot difunctionalization of vinyl arenes using CO₂ and pinacol boranes. Recently, much progress has been made to improve the scope and versatility of boracarboxylation reactions to now include electron-deficient and α-methyl substituted vinyl arenes. However, the potential transformations of boracarboxylated products have remained unexplored. Here, methodologies to transform the β-aryl alkylboronic ester into new C-C, C-N, and C-X bonds will be described. Medically relevant 2,3-diarylpropionic acids can now be accessed via a two-step protocol consisting of boracarboxylation of a vinyl arene followed by a palladium(0)-catalyzed Suzuki cross-coupling. This methodology provides access to both the α- and β-regioisomers independently whereas traditional strategies to access these compounds afford only one regioisomer, and in most cases, a mixture of regioisomers. Interesting biaryl and heterocyclic products can be accessed and to demonstrate the synthetic utility of this protocol, a glucagon receptor antagonist was synthesized in 4 less steps than the previously reported method while maintaining similar yields. The transformative capability of boracarboxylated products is further demonstrated through a base-_x005f_x0002_and external oxidant-free copper(II)-catalyzed amination to generate β²-amino acid derivatives. While the β-carboxylic acid was intolerable to the conditions, protection via esterification or amidation allowed for successful amination of the alkylboronic ester to occur. Amination of two bora-NSAIDs, bora-ibuprofen and bora-naproxen, was successful and a number of cyclic and acyclic amines are suitable for the transformation. Preliminary mechanistic work suggests that this amination does not proceed through a free-radical intermediate but rather a two-electron pathway. Finally, a novel halogenation of boracarboxylated products is achieved to generate the corresponding β-aryl alkyl halides. This methodology is performed in a base, metal, and additive free manner that utilizes cheap and readily available sources of electrophilic halide. Both bromination and iodination are demonstrated and can be achieved on a variety of electron-rich and electron-poor boracarboxylated products and can subsequently undergo amination to provide an alternative route to β²-amino acid derivatives. Mechanistic experiments suggest that the β-carboxylic acid is required to achieve the activation of the C-B bond. Radical trapping experiments also indicate that this transformation may occur through the formation of an alkyl radical although this is unlikely.

Keywords: Boracarboxylation ; alkylboronic ester ; Suzuki cross-coupling ; oxidative amination ; 2,3-diarylpropionic acid ; β²-amino acid

Purchased from AmBeed: 161265-03-8 ; 73183-34-3 ; 128-37-0 ; 1122-58-3 ; 1416881-52-1

Product Details of Butylated hydroxytoluene

CAS No. :	128-37-0
Formula :	C₁₅H₂₄O
M.W :	220.35
SMILES Code :	CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C
Synonyms :	BHT; NSC 6347
MDL No. :	MFCD00011644
InChI Key :	NLZUEZXRPGMBCV-UHFFFAOYSA-N
Pubchem ID :	31404

Safety of Butylated hydroxytoluene

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H315-H319-H360-H373-H410
Precautionary Statements:	P273-P260-P270-P202-P201-P264-P280-P302+P352-P391-P337+P313-P305+P351+P338-P308+P311-P362+P364-P332+P313-P301+P312+P330-P405-P501
Class:	9
UN#:	3077
Packing Group:	Ⅲ

Application In Synthesis of Butylated hydroxytoluene

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 128-37-0 ]

[ 128-37-0 ] Synthesis Path-Downstream 1~10

1
[ 92-52-4 ]
[ 128-37-0 ]
[ 1625-91-8 ]

References: [1]Macromolecules,2005,vol. 38,p. 7950 - 7956.

2
[ 128-37-0 ]
[ 57-88-5 ]
[ 83883-26-5 ]
[ 206053-52-3 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In pyridine; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chloroform; N,N-dimethyl-formamide;	A Cholesteryl 4-(6-acryloyloxyhexyloxy)benzoate STR13 2.92 g (0.01 mole) 4-(6-acryloyloxyhexyloxy)benzoic acid is dissolved in 10 mL CHCl3 and two drops of N,N-dimethylformamide and 30 mg of 2,6-di-tert-butyl-p-cresol were added. Next, 15 mL thionyl chloride was added dropwise to the solution which was stirred at 70° C. until no more gas was given off (approx. 1-2 hours). Then, the CHCl3 and excess thionyl chloride were distilled off under vacuum. The residue is 4-(6-acryloyloxyhexyloxy)benzoyl chloride. The acid chloride was dissolved in 30 mL absolute ether and at 0 to 5° C. added dropwise to 3.86 g (0.01 mole) cholesterol in 10 mL pyridine. It was then stirred for 17 hours at 50° C. For workup, the solution was poured into 200 to 300 mL ice water and acidified with conc. HCl. The product precipitated as a white precipitate. The precipitate was filtered off, washed with saturated NaHCO3 solution, and then with H2 O. It was then recrystallized twice from 100-mL portions of ethanol. After drying, 4.5 g (69percent) white crystals 27 are obtained. Characterization 1 H NMR (CHCl3): 0.65 (s, 3H); 0.8 to 2.1 (m, 46 H); 2.45 (m, 2H); 3.88 (t, 2H); 4.15 (t, 2H); 4.821 (m, 1H); 5.40 (m, 1H); 5.80 (dd, 1H); 6.10 (dd, 1H); 6.38 (dd, 1H); 6.85 (d, 2H); 7.95 (d, 2H) ppm 13 C NMR (CDCl3): 11.82; 18.68; 19.34; 21.01; 22.52; 22.78; 23.80; 24.24; 25.66; 27.95; 28.19; 28.49; 28.96; 31.85; 35.75; 36.15; 36.60; 37.01; 38.25; 39.47; 39.70; 42.47; 50.00; 56.10; 56.64; 64.39; 67.87; 74.12; 113.89; 122.59; 123.05; 128.52; 130.44; 131.46; 139.71; 162.66; 165.69; 166.20 ppm IR (KBr): 2943; 2866; 1717; 1634; 1605; 1510; 1273; 1250; 1198; 1167; 1115; 1007; 772 cm-1

References: [1]Patent: US6049000,2000,A .

3
petroleum [ No CAS ]
[ 72287-26-4 ]
[ 128-37-0 ]
[ 594-27-4 ]
[ 134394-05-1 ]
(+/-)-8-Acetyl-2-(dipropylamino)tetralin hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
323 mg (44%)	With lithium chloride;silica gel; In N-methyl-acetamide;	Example 7 (-)-8-Acetyl-2-(dipropylamino)tetralin hydrochloride A mixture of (-)-2-(dipropylamino)-8-[(trifluromethylsulfonyl)oxyl]tetralin (910 mg, 2.4 mmol), tetramethylstannane (514 mg, 2.88 mmol), lithium chloride (315 mg, 7.44 mmol), dichloro[1,1'-bis(diphenylphosphino) ferrocene]-palladium(ii) [PdCl2 (dppf)] (12 mg, 0.144 mmol), molecular sieves (4 A; 240 mg), 2,6-di-t-butyl-4-methylphenol (catalyst) in dimethylformamide (20 ml) was stirred under an atmosphere of carbon monoxide for 18 h at 90° C. The catalyst was filtered off and the filtrate was partitioned between water and ether. The organic layer was dried (sodium sulfate) and concentrated. The residue was chromatographed on an alumina column eluted with ether/light petroleum 1:16. Pure fractions were pooled and concentrated. The resulting oil was converted into the hydrochloride which was recrystallized from chloroform and ether to afford 323 mg (44percent) of pure (-)-8-acetyl-2-(dipropylamino)tetralin hydrochloride, mp: 114°-116° C. [alpha]D:-123.2° C. (c 1.0, MeOH).

References: [1]Patent: US5635537,1997,A .

4
4-aza-4-methyl-2-phenyl-1,6-heptadiene-3,5-dione [ No CAS ]
[ 128-37-0 ]
[ 122-72-5 ]
3-methyl-1-phenyl-3-azabicyclo[3.1.1]-heptane-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzophenone; In methylene chloride acetone;	(b) 3-Methyl-1-phenyl-3-azabicyclo[3.1.1]heptane-2,4-dione A solution of 50 g of 4-aza-4-methyl-2-phenyl-1,6-heptadiene-3,5-dione, 1.2 g of benzophenone and 0.5 g of 2,6-di-tert-butyl-p-cresol in 2.5 1 of methylene chloride-acetone (1:1) is irradiated for 48 hours with a mercury vapour lamp (HPK 125W; Philips) positioned in a water-cooled Pyrex finger. After evaporation, the crude product is chromatographed with tolueneethyl acetate (9:1) on silica gel 60. The crystalline product thus obtained is recrystallized from diisopropyl ether-methylene chloride: m.p. 175-176 C.

References: [1]Patent: US4883877,1989,A .

5
[ 2651-43-6 ]
[ 128-37-0 ]
[ 100-46-9 ]
[ 13304-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	With PPA;	EXAMPLE 6 N-benzylacrylamide. 59 g of beta-hydroxypropionamide and 75 g of benzylamine were heated with 50 mg of 2,6-di-t-butyl-p-cresol for 7 hours in a temperature range of 120-170 C. until the evolution of ammonia was complete. After adding 2.2 g of polyphosphoric acid distillation was carried out in an oil pump vacuum; the subsequent redistillation with the addition of 1 ml of sulphuric acid yielded 92 g of N-benzylacrylamide, Bp0.1 113 C., which crystallized in the receiver. Mp (crude product): 53 C. NMR (CDCl3): delta=4.35 (d,2); 5.35-6.25 (m,3); 7.2 (s,5).

References: [1]Patent: US4237067,1980,A .

6
[ 85-52-9 ]
[ 128-37-0 ]
[ 119692-59-0 ]
[ 1214748-82-9 ]